Article
Biochemistry & Molecular Biology
Zhi-Wen Liu, Min Song, Jun-Ya Wang, De-Zhi Wang, Biao Sun, Lei Shi, Ren-Wang Jiang, Min Ma, Xiao-Qi Zhang
Summary: Eight unprecedented monoterpenoid indole alkaloid (MIA) adducts and dimers, melofusinines A-H (1-8), and three undescribed melodinus-type MIA monomers, melofusinines I-K (9-11), were isolated from Melodinus fusiformis. Compounds 1 and 2 are hybrid indole alkaloids incorporating an aspidospermatan-type MIA with a monoterpenoid alkaloid unit. Compounds 3-8 are the first MIA dimers constructed through an aspidospermatan-type monomer and a rearranged melodinus-type monomer.
Article
Chemistry, Organic
Tape Kouame, Guillaume Bernadat, Victor Turpin, Marc Litaudon, Aboua Timothee Okpekon, Jean-Francois Gallard, Karine Leblanc, Somia Rharrabti, Pierre Champy, Erwan Poupon, Mehdi A. Beniddir, Pierre Le Pogam
Summary: Melonine is a basic monoterpene indole alkaloid (MIA) skeleton from Melodinus philliraeoides, with its structure revised into an unprecedented MIA scaffold. Proposed DFT-validated biosynthetic paths to both this new core and the originally reported form suggest the thermodynamic feasibility of the original structure of melonine, indicating its potential existence as a natural product.
Review
Chemistry, Medicinal
Tingting Meng, Yani Hou, Congshan Shang, Jing Zhang, Bo Zhang
Summary: Indole derivatives are important antibacterial agents that can act against MRSA and other bacteria; through strategies such as dimerization and hybridization, new potential anti-MRSA agents with antibacterial activity have been discovered.
ARCHIV DER PHARMAZIE
(2021)
Article
Chemistry, Organic
Eunjoon Park, Cheolwoo Bae, Cheon-Gyu Cho, Cheol-Hong Cheon
Summary: The total syntheses of the antirhine alkaloids were achieved through a series of reactions, including the cyanide-catalyzed imino-Stetter reaction and subsequent C-ring formation to generate the key intermediate. The trans-selective installation of the homoallylic alcohol side-chain at C-15 allowed the successful total syntheses of antirhine and its known epimer.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jiahang Yan, Yanxia Zhen, Pengyan Wang, Yimeng Han, Huanhuan Zou, Junhan Chen, Weigang He, Weiqing Xie
Summary: In this study, a de novo synthesis of the bisindole alkaloid geissolosimine was accomplished, along with the synthesis of related compounds and the demonstration of an innovative strategy. These findings provide new insights for further research.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Matteo Faltracco, Said Ortega-Rosales, Elwin Janssen, Razvan C. Cioc, Christophe M. L. Vande Velde, Eelco Ruijter
Summary: The unexpected discovery in a seemingly trivial reaction led to the selective formation of a new carbazole product. This reaction, by carefully varying substituents, revealed a complex cascade mechanism with at least 10 elementary steps that could be directed towards different carbazole derivatives.
Article
Chemistry, Organic
Chao Liu, Luc Van Meervelt, Vsevolod A. Peshkov, Erik V. Van der Eycken
Summary: A novel gold-catalyzed hydroarylation/Michael addition process has been developed for the efficient construction of benzazepinoindole polycyclic scaffolds from readily accessible multifunctional Ugi adducts. The developed methodology exhibits a broad substrate scope, excellent functional-group tolerance, and high yields of the target benzazepinoindoles.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Plant Sciences
Nelson Jeng-Yeou Chear, Francisco Leon, Abhisheak Sharma, Siva Rama Raju Kanumuri, Grant Zwolinski, Khalil A. Abboud, Darshan Singh, Luis F. Restrepo, Avi Patel, Takato Hiranita, Surash Ramanathan, Aidan J. Hampson, Lance R. McMahon, Christopher R. McCurdy
Summary: This study isolated and characterized ten indole and oxindole alkaloids from Malaysian Kratom leaves, and assessed their binding affinity at opioid receptors. Certain oxindole alkaloids showed high binding affinity and greater analgesic efficacy than morphine in rats, indicating their potential therapeutic activity.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Multidisciplinary
Maciej Monedeiro-Milanowski, Fernanda Monedeiro, Pawel Pomastowski
Summary: A study found that a diverse silver-lactoferrin complex exhibited a synergistic antibacterial effect and was more lethal than lactoferrin alone. Gas chromatography-mass spectrometry and mass spectrometry analysis revealed that the complex induced metabolic shifts and protein changes in bacteria, indicating stress, respiratory exhaustion, and oxidative stress. This study provides valuable insights into the antimicrobial mechanisms of the complex.
Article
Plant Sciences
Emmanuel O. Adeyoju, Clement O. Ajayi, Awodayo O. Adepiti, Anthony A. Elujoba
Summary: This study compared the antimalarial activity of methanol and water extracts of MAMA Powder against Plasmodium berghei-infected mice, finding that the water extract exhibited higher efficacy and can be optimized for chloroquine-resistant malaria, aiding in the production of various dosage forms.
JOURNAL OF ETHNOPHARMACOLOGY
(2022)
Review
Oncology
Md. Al Amin, Talha Bin Emran, Jishan Khan, Mehrukh Zehravi, Indu Sharma, Anasuya Patil, Jeetendra Kumar Gupta, D. Jeslin, Karthickeyan Krishnan, Rajib Das, Firzan Nainu, Irfan Ahmad, Polrat Wilairatana
Summary: This review evaluates the impact of indole alkaloids on the Mitogen-activated protein kinase (MAPK) signaling pathway in cancer treatment. Indole alkaloids have strong anticancer properties and research is ongoing to develop new anticancer small molecules. Clinical trials have also shown the potential of indole alkaloids in cancer treatment.
Article
Chemistry, Multidisciplinary
Cheng Li, Bin Zhao, Guojiang Mao, Guo-Jun Deng
Summary: In this study, a Rh(iii)-catalyzed intermolecular regioselective dearomative spirocyclization of 2-aryl-3-nitrosoindoles with alkynes was developed, leading to the redox-neutral and atom-economic construction of spiroindoline-3-one oximes bearing a C2 spirocyclic quaternary carbon center under mild conditions. Both aryl alkyl alkynes and 1,3-diynes generally reacted smoothly in the reaction with moderate to good regioselectivities. DFT calculations provided detailed insights into the reaction mechanism and explained the origins of the regioselectivities.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Daojiang Yan, Kunya Wang, Songlin Bai, Bingyu Liu, Jian Bai, Xiangbing Qi, Youcai Hu
Summary: This study reports a novel mechanism for the formation of 1,2-oxazine by Meisenheimer rearrangement, providing a new example of rearrangement reactions in the biosynthesis of natural products, and offering a new strategy for the discovery of natural products with N-O tethers through genome mining.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Yiting Zheng, Yuen Tsz Cheung, Lixin Liang, Huiying Qiu, Lei Zhang, Anson Tsang, Qing Chen, Rongbiao Tong
Summary: This study reports an electrochemical method for the oxidative rearrangement of tetrahydro-beta-carbolines. By using a multifunctional LiBr electrolyte and a zero-gap flow cell, bioactive spirooxindoles can be synthesized efficiently without using hazardous oxidants.
Article
Pharmacology & Pharmacy
Liliana Raimundo, Angela Paterna, Juliana Calheiros, Joana Ribeiro, David S. P. Cardoso, Ilaria Piga, Susana Junqueira Neto, Denise Hegan, Peter M. Glazer, Stefano Indraccolo, Silva Mulhovo, Jose Luis Costa, Maria-Jose U. Ferreira, Lucilia Saraiva
Summary: The study demonstrates that BBIT20, a natural compound, inhibits homologous DNA repair in triple-negative breast and ovarian cancer cells, leading to DNA damage and apoptosis. BBIT20 shows significant antitumor activity in patient-derived cells and xenograft mouse models of ovarian cancer, with low toxicity in non-malignant cells and undetectable side effects in mice. Additionally, BBIT20 does not induce resistance and exhibits synergistic effects with cisplatin and olaparib in 2D and 3D models of these cancer cells.
BRITISH JOURNAL OF PHARMACOLOGY
(2021)
